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1-Hydroxybenzotriazole → HCID 178523538, compound

HRID 1178145
Notes
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Reaction equation

HRID 1178145 reaction equation
C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.[C:21]1([C:27]2[NH:31][N:30]=[C:29]([C:32]([OH:34])=O)[CH:28]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCN=C=NCCCN(C)C.Cl.[NH2:47][CH2:48][C:49]([N:51]1[CH2:56][CH2:55][N:54]([C:57](=[O:68])[C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=2[C:64]([F:67])([F:66])[F:65])[CH2:53][CH2:52]1)=[O:50]>CN(C=O)C.O>[O:50]=[C:49]([N:51]1[CH2:52][CH2:53][N:54]([C:57](=[O:68])[C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=2[C:64]([F:67])([F:66])[F:65])[CH2:55][CH2:56]1)[CH2:48][NH:47][C:32]([C:29]1[CH:28]=[C:27]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:31][N:30]=1)=[O:34]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 595596292-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanoneHCID 178479739HCID 178479739, compound

Product 1

HCID 178523538
HCID 178523538, compound
Yield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

HOBt (45 mg, 0.33 mmol) and DIPEA (137.5 mg, 1.06 mmol) were added to a stirred solution of 5-phenyl-1H-pyrazole-3-carboxylic acid hydrochloride (50 mg, 0.22 mmol) in DMF (1.0 mL). The reaction mass was cooled to 10° C. and EDCI.HCl (64 mg, 0.33 mmol) was added, followed by the addition of 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone (as TFA salt) (125 mg, 0.29 mmol). The resulting mixture was stirred at room temperature overnight. The mixture was then diluted with water and the resulting precipitate was filtered and dried in vacuo to afford 5-phenyl-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide as a solid product in 62% yield, LC-MS purity: 99.127%, 1H NMR (DMSO): δ 13.6 (s, 1H), 8.1 (s, 1H), 7.7 (m, 5H), 7.4 (m, 4H), 7.1 (s, 1H), 4.1 (m, 2H), 3.6 (m, 4H), 3.4 (m, 2H), 3.2 (m, 2H).

Workup

  1. filtrationthe resulting precipitate was filtered
  2. customdried in vacuo

Sources & evidence

ORD record
ord-f81e1cfb6d754fc1970834f78c88b329
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07842696B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes